Antiatherosclerotic furochromones and intermediates therefor

ABSTRACT

The present invention particularly provides novel furochromones and intermediates for their preparation.

CROSS REFERENCE TO RELATED APPLICATIONS

This is a division of application Ser. No. 378,686, filed 17 May 1982, now issued as U.S. Pat. No. 4,459,420 on 10 July 1984.

BACKGROUND OF THE INVENTION

The present application relates to novel furochromone compounds which are useful in the treatment of atherosclerosis. The use and preparation of these compounds is described in application Ser. No. 378,686, filed 17 May 1982, which is incorporated herein by reference.

PRIOR ART

Methods of the total synthesis of khellin are known, as are certain chemical intermediates useful in its synthesis.

The use of pyrogallol in the synthesis of khellin intermediates is known. For example, the transformation of pyrogallol to the khellin intermediate 1-(2,3-dihydro-6,7-dihydroxy-5-benzofuranyl)ethanone is known. The parahydroxylation of this intermediate is also known. See Row, L. R., et al., Indian J. Chem., 5:105 (1967) describing this transformation and the subsequent dimethylation to yield known khellin intermediates. U.S. Pat. No. 4,284,569 provides a variety of novel anti-atherosclerotic furochromones.

SUMMARY OF THE INVENTION

The present invention particularly provides:

(a) a benzofuran of formula III wherein R₂ is C₁ -C₄ alkyl;

(b) a benzofuran of formula IV wherein R₅ is C₂ -C₄ alkyl;

(c) a benzofuran of formula V wherein one of R₆ and R₇ is C₁ -C₄ alkyl and the other is C₂ -C₄ alkyl with the proviso that R₆ and R₇ are different; and

(d) an anti-atherosclerotic furochromone of formula VI wherein one of R₆ and R₇ is C₁ -C₄ alkyl and the other is C₂ -C₄ alkyl with the proviso that R₆ and R₇ are different; wherein R₁₂ is --CH₂ --S(O)_(n) --R₂₀, wherein n is zero, one or two and R₂₀ is C₁ -C₅ alkyl;

wherein R₁₃ is:

(1) hydrogen; or

(2) chloro, iodo, or bromo.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

The present invention particularly provides 4-Ethoxy-9-methoxy-7-methylthiomethylfurochromone and 4-Methoxy-9-ethoxy-7-methylthiomethylfurochromone. 

I claim:
 1. An anti-atherosclerotic furochromone of formula VI:wherein one of R₆ and R₇ is C₁ -C₄ alkyl and the other is C₂ -C₄ alkyl with the proviso that R₆ and R₇ are different; wherein R₁₂ is --CH₂ --S(O)_(n) --R₂₀, wherein n is zero, one or two and R₂₀ is C₁ -C₅ alkyl; wherein R₁₃ is:(1) hydrogen, or (2) chloro, iodo or bromo.
 2. 4-Ethoxy-9-methoxy-7-methylthiomethylfurochromone, a compound according to claim
 1. 3. 4-Methoxy-9-ethoxy-7-methylthiomethylfurochromone, a compound according to claim
 1. 